1: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 2: p-toluenesulfonic acid / methanol / 1 h / 20 °C 3: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 4: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 5: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C 6: 1.) H2, quinoline, 2.) H2O / 1.) Lindlar's cat. / 1.) AcOEt View Scheme

1: (i) EtMgBr, THF, (ii) /BRN= 1754010/, CuCN 2: H2, quinoline / Lindlar catalyst / ethanol / 20 °C View Scheme

1: CuI, NaI, K2CO3 / dimethylformamide / 5 h / 20 °C 2: H2 / Lindlar catalyst, quinoline View Scheme

1: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 2: p-toluenesulfonic acid / methanol / 1 h / 20 °C 3: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C View Scheme

1: CuI, NaI, K2CO3 / dimethylformamide / 5 h / 20 °C 2: 89 percent / 5percent aq. LiOH / methanol / 2 h / Ambient temperature View Scheme

1: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 2: p-toluenesulfonic acid / methanol / 1 h / 20 °C 3: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 4: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 5: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C View Scheme

1: (i) EtMgBr, THF, (ii) /BRN= 1754010/, CuCl 2: PBr3, Py / diethyl ether / Heating 3: CuCl / tetrahydrofuran 4: H2, quinoline / Lindlar catalyst / ethanol View Scheme

1: CuI, NaI, K2CO3 / dimethylformamide / 5 h / 20 °C 2: H2 / Lindlar catalyst, quinoline 3: 5percent aq. LiOH / methanol / 2 h / Ambient temperature View Scheme

1: 1.) EtMgBr, 2.) CuI / 1.) THF, 23 deg C, 10 h, 2.) THF, 23 deg C, 2 h 2: 91 percent / H2 / 10percent Pd/BaSO4, quinoline / ethyl acetate / 0.75 h / 23 °C / 760 Torr 3: 93 percent / Br2, 1,2-bis(diphenylphosphino)ethane / CH2Cl2 / 9 h / 23 °C View Scheme